(6-Methoxypyridin-3-yl)boronic acid → HCID 178488513, compound

HRID 2047514Notes

Reaction equation

HRID 2047514 reaction equation
Br[C:2]1[CH:20]=[CH:19][C:5]2[N:6]=[C:7]([C@H:9]3[CH2:12][C@H:11]([N:13]4[CH2:17][CH2:16][CH2:15][C@H:14]4[CH3:18])[CH2:10]3)[S:8][C:4]=2[CH:3]=1.[CH3:21][O:22][C:23]1[N:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1.N1C=C(B(O)O)C=NC=1>>[CH3:21][O:22][C:23]1[N:28]=[CH:27][C:26]([C:2]2[CH:20]=[CH:19][C:5]3[N:6]=[C:7]([C@H:9]4[CH2:12][C@H:11]([N:13]5[CH2:17][CH2:16][CH2:15][C@@H:14]5[CH3:18])[CH2:10]4)[S:8][C:4]=3[CH:3]=2)=[CH:25][CH:24]=1

Participants

4

Reactant 3

HCID 2734368(6-Methoxypyridin-3-yl)boronic acidHCID 2795193(Pyrimidin-5-yl)boronic acidHCID 178461421HCID 178461421, compound

Product 1

HCID 178488513HCID 178488513, compound

Procedure

The title compound was prepared according to the procedure described in Example 1F, except for substituting the product of Example 11A for the product of Example 1E and substituting 6-methoxy-3-pyridineboronic acid for pyrimidine-5-boronic acid. 1H NMR (500 MHz, CDCl3) δ ppm 8.43 (d, J=2.18 Hz, 1H) 8.03 (d, J=8.42 Hz, 1H) 7.97 (d, J=1.56 Hz, 1H) 7.83 (dd, J=8.58, 2.65 Hz, 1H) 7.61 (dd, J=8.42, 1.56 Hz, 1H) 6.84 (d, J=8.73 Hz, 1H) 4.00 (s, 3H) 3.81-3.92 (m, 1H) 3.47-3.58 (m, 1H) 2.97-3.15 (m, 1H) 2.66-2.85 (m, 2H) 2.44-2.64 (m, 2H) 2.26-2.39 (m, 1H) 1.92-2.03 (m, 1H) 1.79-1.89 (m, 1H) 1.67-1.77 (m, 1H) 1.46-1.64 (m, 2H) 1.14 (d, J=5.30 Hz, 3H). MS: (M+H)+=380.

Sources & evidence

ORD record
ord-47ffab51b3604e0da71cd2f32c0e83a8
Source dataset
uspto-grants-2013_11
Patent number
US08592467B2

Reaction notes

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